The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Action of aluminum chloride on esters of polyatomic alcohols》. Authors are Sivertsev, A. P..The article about the compound:2-Chloroethyl acetatecas:542-58-5,SMILESS:CC(OCCCl)=O).Quality Control of 2-Chloroethyl acetate. Through the article, more information about this compound (cas:542-58-5) is conveyed.
Summary of a thesis. Heating an equimolar mixture of AlCl3 and (AcOCH2)2 1 h. to 150-60° gave ClCH2CH2OAc, b. 142-8°, and ClAl(OAc)2, a glassy mass (after washing with benzene and Et2O). Similar treatment of (BzOCH2)2 gave ClCH2CH2OBz, b17 139-40°, 20201783, nD20 1.5233, and ClAl(OBz)2. Similar reaction of an equimolar mixture of AlCl3 with triacetin gave ClCH2CH(OAc)CH2OAc, b20 125-30°, d2020 1.2018, nD20 1.4393; the use of 0.5 mol triacetin gave ClCH2CHClCH2OAc, b20 90-5°, d2020 1.2733, nD20 (not given); the AlCl3 was found to have been transformed into ClAl(OAc)2. Further heating of the dichloropropyl acetate with AlCl3 failed to produce further reaction. Pentaerythritol tetra-acetate (1 mol) heated as above with 0.5 mol AlCl3 gave ClCH2C(CH2OAc)3, b4.5 152-60°, d2020 1.2272, nD20 1.4587; an equimolar mixture gave (ClCH2)2C(CH2OAc)2, b6 146-8°, d2020 1.268, nD20 1.4681; 0.5 mol of the ester to 1 mol AlCl3 gave (ClCH2)3CCH2OAc, b8 126-7°, d2020 1.3111, nD20 1.4832. The Al is transformed into ClAl(OAc)2. Hydrolysis of the chlorides, followed by acetylation, gave the original tetraacetate, showing that no changes of the skeleton took place. Thus, AlCl3 is incapable of replacing all OAc groups by Cl in polyacetate esters of polyat. alcs.; 1 ester group always remains intact.
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